Direct fluorination of etherified or unetherified hydroxy group bearing aromatic compounds

Abstract

A process for direct fluorination of etherified or unetherified hydroxy group-bearing aromatic compounds, which comprises reacting an etherified or unetherified hydroxy group-bearing aromatic compound with fluorine gas to give the corresponding etherified or unetherified hydroxy group and at least one fluorine atom-bearing aromatic compound.

What is claimed is: 
     
       1. A process for the direct fluorination of hydroxy group-bearing aromatic compounds which comprises reacting a hydroxy group-bearing aromatic compound with fluorine gas in an inert solvent at a temperature of from -40° to 10° C. to give the corresponding product having at least one hydroxy group and at least one fluorine atom thereon. 
     
     
       2. The process according to claim 1, wherein the inert solvent is acetonitrile, a glyme or a halogenated hydrocarbon or a mixture thereof. 
     
     
       3. The process according to claim 2, wherein the glyme is diglyme, triglyme or tetraglyme. 
     
     
       4. The process according to claim 1, wherein the fluorine gas is diluted with an inert gas prior to reaction with said hydroxy group-bearing aromatic compound. 
     
     
       5. The process according to claim 1, wherein the aromatic compound reactant is a compound comprising an aromatic ring having at least one hydroxy group thereon. 
     
     
       6. The process according to claim 5, wherein said aromatic ring is a benzene ring. 
     
     
       7. The process according to claim 5, wherein the aromatic compound reactant is represented by the formula: ##STR3## wherein R, R' and R" are each hydrogen, halogen, lower alkoxy, hydroxy, nitro, cyano, formyl, phenyl, hydroxyphenyl or lower alkoxyphenyl. 
     
     
       8. The process according to claim 1, wherein said product is represented by the formula: ##STR4## wherein R, R' and R" are each hydrogen, halogen, lower alkyl, lower alkoxy, hydroxy, nitro, cyano, formyl, phenyl, hydroxyphenyl or lower alkoxyphenyl. 
     
     
       9. The process according to claim 1, wherein the aromatic compound reactant has at least one open position with no substituent on at least one of the ortho and para positions to said hydroxy group and said product has a fluorine atom on at least one of said open positions.